The host of The Deep Wealth Podcast, Jeffrey Feldberg, speaks with two remarkable guests, AJ Wasserstein and an entrepreneur who prefers to go by the pseudonym “Retired Founder”. This post-exit round table discussion peels back the layers on what life truly looks like after a successful business exit and offered valuable perspectives for current and aspiring entrepreneurs.
AJ Wasserstein, a distinguished lecturer at the Yale School of Management and a seasoned entrepreneur, along with Retired Founder, shared their journeys and lessons learned after exiting their businesses. It’s a path less talked about but one that holds both immense opportunity and unforeseen challenges.
AJ Wasserstein reflected on his initial post-exit experience, stating, “The biggest mistake most people make after they exit a company is to immediately jump into new ventures, boards, or investments without taking a meaningful pause.” He emphasized the importance of resisting the urge to fill the void left by the exit with immediate action. Instead, embracing a period of reflection and self-examination is crucial.
Retired Founder shared his journey of self-discovery, admitting to the challenging transition from being at the helm of a thriving business to finding a new sense of purpose. He said, “It took me almost four years into retirement to hit a wall… I realized that the possessions and lifestyle I had amassed post-exit were not bringing me happiness.”
Entrepreneurs work tirelessly toward the dream of a successful exit, envisioning it as the ultimate goal. However, what comes afterwards can often feel like uncharted territory. AJ Wasserstein and Retired Founder share their journeys, revealing that the aftermath is not always as fulfilling as anticipated. Their stories serve as a testament to a common, but seldom discussed, experience among entrepreneurs: the post-exit blues.
Both guests reveal how their initial expectations of a carefree, luxurious life post-exit were quickly met with the realization that something deeper was amiss. They highlight the struggle to find new identities and purposes beyond their business achievements.
Discovering New Callings and Identities
Both guests touched on the importance of redefining one’s identity and scorecard post-exit. AJ discussed the value of introspection and re-evaluating what truly matters in life beyond financial success. “Figuring out your new scorecard is essential. It’s about understanding what will drive you forward now that the traditional metrics of business success no longer apply.”
Retired Founder highlighted the concept of seeking out activities and commitments that provide energy and purpose rather than draining it. “Instead of focusing on achievements or material possessions, I started looking for things that give me energy,” he shared. This approach led him to work on creating a community for post-exit entrepreneurs, focusing on sharing and overcoming the collective challenges faced after exiting a business.
Many entrepreneurs envision their exit as the ultimate finish line, the point at which they can finally say they’ve made it. However, as Wasserstein and the Retired Founder reveal, this supposed endgame often introduces a new set of challenges that are rarely anticipated.
“You’re sort of this odd duck… when all of a sudden you don’t have to go to work or you’re in a situation where you’re not going to work, you’re in a weird place,” says AJ Wasserstein, capturing the essence of stepping into an unstructured life post-exit.
The Retired Founder mirrors this sentiment, emphasizing the emotional rollercoaster that follows the exit. “You end up talking a lot more about your feelings than the dollars… even those who exited for spectacular amounts of money end up disappointed somehow,” he shares.
The Vital Step of Pausing and Reflecting
A common theme from both entrepreneurs was the significance of taking a step back before moving forward. AJ elaborated on this, “Pause, reflect, and then operationalize. Take a sabbatical if you can. Let go of the past, celebrate your achievements, and then slowly start contemplating your next moves.”
Retired Founder echoed the sentiment, expressing how changing the ingrained habits and mindsets that made him successful as an entrepreneur was crucial to finding happiness post-exit. “Recognizing and shutting down those subroutines in my brain that were no longer serving me made all the difference.”
Despite the unexpected emptiness that may follow an exit, both Wasserstein and the Retired Founder acknowledge the unique gift that this phase offers – the luxury of time and financial freedom. However, they stress the importance of using this gift wisely by engaging in deep self-examination and considering a broad array of possibilities for one’s true calling.
“It’s a blessing and a genuine gift to be able to architect a life in any desired manner. Although not easy, this is a worthwhile process to invest energy into getting right,” advises AJ Wasserstein, promoting the idea that post-exit life should be a deliberate construction, not a void filled with aimless distractions.
AJ Wasserstein advises entrepreneurs to resist the rush into new ventures, boards, or investments right after their exit. He underscores the value of taking a deliberate pause to process the change, mourn the loss of one’s entrepreneurial identity, and celebrate the achievements. This pause allows for the space needed to contemplate what truly matters moving forward.
Crafting a Life by Design, Not Default
AJ and Retired Founder’s experiences underscore the untold complexities and emotional journeys of life after a business exit. They both advocate for a deliberate and thoughtful approach to this phase, stressing the importance of crafting a life by intention rather than by inertia.
AJ reminded us, “Being a post-exit entrepreneur truly is a gift and a blessing,” urging listeners to embrace the opportunities to architect a new life with purpose and fulfillment at its core.
Retired Founder’s advice to get on offense, to be proactive rather than reactive in designing the next chapter, speaks to the heart of navigating post-exit life successfully.
One of the greatest challenges mentioned is discovering a new purpose that matches the intensity and fulfillment of building and exiting a successful business. According to Retired Founder, the quest for a new purpose can be both daunting and illuminating.
“It’s going to be okay. Maybe a little better than okay, but it’s about finding that joy in the journey again, not just the destination,” Retired Founder reflects, suggesting that fulfillment comes from embracing the process of self-discovery and setting intentional goals.
Both entrepreneurs advocate for setting aside time to genuinely reflect on personal values, exploring different career arcs, and allowing for trial and exploration without the pressure to commit immediately.
Retired Founder echoes the notion of reevaluating life’s priorities, sharing his journey of replacing the void left by his business ventures with meaningful relationships and hobbies. He talks about the mistake of seeking fulfillment in material possessions and status symbols, only to find true satisfaction in simpler, more authentic experiences.
Strategic Reflection: A Dozen Questions to Consider After Selling Your Business
AJ Wasserstein introduces the concept of the “A Dozen Questions to Consider After Selling Your Business,” a guide designed to help entrepreneurs navigate post-exit life. These questions encourage deep introspection about personal values, future aspirations, and the kind of legacy one wishes to leave. They serve as a tool for transitioning from a purely business-focused mindset to a more holistic view of success and happiness.
The conversation shifts to the critical issue of finding balance after the exit. Retired Founder shares insights on the importance of not allowing wealth to dictate one’s life direction, emphasizing the roles of passion, purpose, and relationships in crafting a fulfilling post-exit life. AJ adds that true happiness often lies in meaningful engagements and contributions to society, rather than in the accumulation of wealth.
Here are twelve pivotal questions derived from our podcast guests’ experiences that every entrepreneur should ponder after exiting their business:
1. What Do I Want My Eulogy to Be?
Reflecting on your eulogy allows you to focus on the legacy you wish to leave behind, going beyond financial success to the values and relationships that define you.
2. How Will More Money Change My Life?
Consider the true impact of additional wealth. Will it genuinely enhance your happiness, or could it introduce unforeseen complexities?
3. What is My New Scorecard?
Identify new metrics for measuring success in your post-exit life. Is it personal growth, community impact, or perhaps, new entrepreneurial ventures?
4. Am I the Same Person I Was 25 Years Ago?
Acknowledge how you have evolved over time. This realization can influence your future paths and the opportunities you pursue.
5. What Is My Ikigai?
Explore the Japanese concept of *Ikigai* – the intersection of what you love, what you are good at, what the world needs, and what you can be paid for.
6. Why Am I Still Working?
For those continuing to chase professional achievements, it’s crucial to understand the underlying motives. Is it passion, purpose, or something else?
7. What Brings Joy and Fulfillment?
Pursue activities and causes that genuinely bring you happiness and a sense of fulfillment.
8. How Do I Redefine Success?
In the absence of business goals, find new ways to define and achieve success on your terms.
9. How Can I Contribute to Society?
Look for meaningful ways to use your experience, knowledge, and resources to make a positive impact on others.
10. What Are My Passions Outside of Work?
Rediscover hobbies and interests that may have been sidelined during your entrepreneurial journey.
11. Who Is My Support System?
Identify friends, family, and peers who will provide support, advice, and companionship as you navigate post-exit life.
12. How Do I Want to Be Remembered?
Beyond professional accomplishments, consider the personal qualities and actions you want to be remembered for.
Conclusion: Embracing the Post-Exit Journey
The insights shared by AJ Wasserstein and Retired Founder provide invaluable lessons for any entrepreneur contemplating or navigating life after an exit. It’s a journey that requires patience, introspection, and a willingness to redefine success on new terms.
As we reflect on their experiences and wisdom, it’s clear that the post-exit life isn’t a linear path to “happily ever after” but an opportunity to explore deeper meanings, connections, and purposes. The true gift lies not in the financial freedom achieved but in the freedom to rediscover oneself and contribute to the world in new and meaningful ways.
AJ Wasserstein beautifully summed up the essence of this transition, “It’s all about enjoying every moment and prioritizing the relationships and health that truly matter. In the end, that’s what fills your life with joy and purpose.”
And as Retired Founder wisely put it, “It’s going to be okay, regardless of the ups and downs. Have confidence in your ability to navigate through it, and remember, the best parts of your journey may just be ahead of you.”
Life after a liquidity event is not the fairytale ending many entrepreneurs fantasize about; it is, however, an opportunity to embark on a journey of personal growth and discovery. The insights shared by AJ Wasserstein and the Retired Founder serve as a powerful reminder that the true essence of wealth lies not in the material success but in the depth of one’s life journey and the impact one chooses to create.
This conversation serves as a poignant reminder that the end of one chapter is merely the beginning of another, rich with potential for growth, discovery, and fulfillment beyond anything previously imagined.
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